Windsor Holiday Rentals from AU$253: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Windsor has to offer?

Private and Calming Waterfront to the Rescue! : This holiday home rental outside Windsor is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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Holiday Rentals in Windsor

"We loved our stay in this beautiful home. Very comfortable, clean and so much attention to detail. The view was both serene and lovely."

"Accurate listing, great location (easy drive to Augusta for dinner), really peaceful and quiet. GPS had a minor problem right at the end trying to send us through a neighbor's trailer, but we figured it out (the external pictures helped). Loved our stay there, even though it was just overnight on the way to somewhere else. Next time, we'll stay for a week."

"The house was really nice. Updated with all modern appliances and very clean. The beds were very comfy. The scenery is beautiful on the lake. Wish there was coffee for the morning but wasn’t replaced from the previous tenants. Overall definitely recommend. "

includes taxes & fees

12 Feb - 13 Feb

"Property was exactly as listed - view of the lake from the deck and living rooms was beautiful. Host was very available and responsive. We had a wonderful time - there were 3 generations of our family with up to 14 members staying at the home. We also hosted a larger family get-together with an additional 10 people for an afternoon with permission from the host. Everyone was impressed with the house, property, lake views, deck and dock. Four of our young adult cousins stayed in the log cabin...

"The house was great in every way. "

"The cabin was so ingeniously set up with battery packs for lighting and plenty of wood for the stove. It gave it an even cozier feel. The land is beautiful and the lake was amazing to look at especially frozen over. I’m so excited to see what the owners do with the property since they are currently developing it. The lake looked stocked with canoes and there is a cute, sturdy dock and places to sit and admire the water in the warmer months. The host was very communicative and gave us...

includes taxes & fees

27 Jan - 28 Jan

"Comfortable, clean, good amenities. Fun home layout for family gathering."

includes taxes & fees

26 Jan - 27 Jan

"This was just what we needed. Right on the water, quiet surroundings and the neighbors were so nice they brought us fresh vegetables."

"Very nice property that is clean and well managed "

"We usually rent right near our relatives closer to Newcastle, but there was a problem with heat in property so we needed a new rental to move into and “Otterly getaway” was willing to rent to us the day before they technically were available which was good for us. The kitchen of the getaway is just perfect for cooking side dishes for our large family Thanksgiving that was just about 20 minutes a way. We slept in the king bed and it was excellent sleeping. The heating system kept us also very...

includes taxes & fees

26 Jan - 27 Jan

" We enjoyed the view from the moon on the lake to the snowfall. Everything was close by if needed."

"We stayed at the property for a trade show with our team and enjoyed a comfortable clean and amazing overall stay. The house was clean kept and the owner was easy to deal with would highly recommend "

"Very good stay."

"Loved this place. Amazing quiet location with so many water toys and activities. Had zero need to leave the whole weekend because there was so much to do there. "

"This house has a beautiful location. My husband and I stayed for a weekend getaway and enjoyed our stay. One issue that we had was the water pressure. It was hard to shower because the water kept going in and out. As others have stated, the inside of the house could use some TLC. Some of the decorations are falling apart on the wall. The paint on the walls in some rooms look incomplete. Overall it was a good stay. "

"Amazing property! "

"Excellent and clean cabin. Had everything we needed. The owner was great and even helped us out at 7am when we locked ourselves out! He came right away. Would highly recommend "

"Comfortable, quiet location. Appreciated the many nightlights. Both showers need grab bars. Basement shower drain not attached to shower floor."

"Peaceful and relaxing. A few things would have been nice to know ahead of our trip. Difficult to get to the water to swim. Did not know when trash pick up was scheduled and had to remind owner that it was not picked up. All that being said - it was very enjoyable"

"Beautiful location right on the water!"

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Other types of properties in Windsor you may be interested in

Indoor pool, seasonal outdoor pool, pool loungers

"I always enjoy staying here."

includes taxes & fees

26 Jan - 27 Jan

Full-sized fridge, microwave, oven, stovetop

"Breakfast awesome. Breakfast staff amazing. My only down side was no water in workout room and no cleaner to wipe down the exercise equipment before and after use. Also. The pool is COLD. Other than that i loved it here "

includes taxes & fees

21 Feb - 22 Feb

"Staff was awesome. Bar / restaurant lady was even better. 10 out of 10 would stay there again. See you in 1 year"

includes taxes & fees

26 Jan - 27 Jan

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$253 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Windsor Holiday Home Travel Info

Number of holiday homes	2
Popular accommodation	Windsor private holiday homes
Known landmarks	Natanis Golf Course, Viles Arboretum and Pine Tree State Arboretum
International airports	Augusta, ME (AUG-Augusta State) and Portland, ME (PWM-Portland Intl. Jetport)

Recent reviews of Windsor properties

5/5 Excellent

"Breakfast awesome. Breakfast staff amazing. My only down side was no water in workout room and no cleaner to wipe down the exercise equipment before and after use. Also. The pool is COLD. Other than that i loved it here "

A verified traveller stayed at Homewood Suites by Hilton Augusta

Posted 2 days ago

5/5 Excellent

Arrived late after a long drive

"I traveled from 5hrs south to attend a funeral service the following morning and arrived after 11pm. The instructions were clear and easy to retrieve the key for the room. I never saw one person since I left fairly early around 8:30am. There wasn’t much for breakfast but I didn’t expect much since it’s probably their off season and it didn’t seem there were many people at the hotel. The only complaint I had was that the room was so incredibly cold maybe 30 to 40° No heat was turned on. There were two monitor heaters in the room and it took a while to warm up so I sat in my vehicle for about 20minutes while I waited. By morning it was cozy and warm. The room was very clean and the bed and pillows were very very comfortable! I would definitely stay again but I’d call ahead to make sure someone turned the heat on…even just at 60 or 65° would be acceptable. "

A verified traveller stayed at Cod Cove Inn, BW Signature Collection

Posted 3 days ago

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its shopping and restaurants.

What are some of the best holiday rentals that Windsor has to offer?

Private and Calming Waterfront to the Rescue!: This holiday home rental outside Windsor is located on a lake, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Maine State Museum, or get outside and enjoy nature at Capitol Park. In the wider area, you’ll find Maine State House and Damariscotta Lake.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.

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Windsor Holiday Rentals

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Holiday Rentals in Windsor

A Charming Waterfront Cottage with Touches of Elegance

A Charming Waterfront Cottage with Touches of Elegance

March Special, Ice Fishing, Dog Friendly

March Special, Ice Fishing, Dog Friendly

Lighthouse Lane

Lighthouse Lane

Luxurious lakefront home with 750' of spectacular frontage on Great Pond

Luxurious lakefront home with 750' of spectacular frontage on Great Pond

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Spacious Country Home w/ Hot Tub, near Colby/Thomas

Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

Tiny Cabin on 100 Acres Kayaks/Canoes/Paddleboards

Camp Lintonia on Tacoma Lakes

Camp Lintonia on Tacoma Lakes

Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok

Lakefront cabin with private dock, wood stove, firepit, deck, & grill - 1 dog ok

Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock

Big Pines Cabin: A Waterfront Retreat Open 4 Seasons, with Private Dock

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

“Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Cottage on Cobbosseecontee Lake. Dates available.

Cottage on Cobbosseecontee Lake. Dates available.

Private and Calming Waterfront to the Rescue!

Private and Calming Waterfront to the Rescue!

Cozy Long Pond Cottage: private mooring & shared dock

Cozy Long Pond Cottage: private mooring & shared dock

Kayakers’ Cabin- “Maine Cabin Masters” remodel.

Kayakers’ Cabin- “Maine Cabin Masters” remodel.

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak

Nature lovers Paradise your own island

Nature lovers Paradise your own island

Cabin China Lake

Cabin China Lake

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Secluded escape with three beaches, lake access, grill & fast WiFi - dogs OK

Rustic, lakefront fishing cabin on Webber Pond with sunset views - 2 dogs OK

Rustic, lakefront fishing cabin on Webber Pond with sunset views - 2 dogs OK

on gorgeous Great Pond (lake), great for families!

on gorgeous Great Pond (lake), great for families!

Other types of properties in Windsor you may be interested in

Senator Inn & Spa

Senator Inn & Spa

Homewood Suites by Hilton Augusta

Homewood Suites by Hilton Augusta

Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

Find out more about Windsor

Find out more about Windsor

Windsor Holiday Home Travel Info

Recent reviews of Windsor properties

Recent reviews of Windsor properties

Homewood Suites by Hilton Augusta

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions